Recalculating Employee Benefits for 2022 with Lindsey Pollak

Leslie Harding
June 7, 2021

Lindsey Pollak is a New York Times bestselling author, keynote speaker, and expert on today’s ever changing, multi-generational workforce. Her most recent book, Recalculating, is an inspirational, practical, and forward-looking career playbook for recent grads, career changers, and transitioning professionals looking to survive and thrive in today’s rapidly evolving employment and work landscape. She joins us to share what she’s learned about today’s changing workplace, the impact of the COVID-19 global pandemic on your employees, and what all this means for your 2022 employee benefits strategy.

Lindsey’s Journey to Becoming a Workplace and Career Expert 

Lindsey’s career path started back in college where she was an RA and found that she loved helping others. After she graduated she struggled to find her path, but she ended up at She wrote Getting From College to Career to provide other young people with the advice she wished she had when she was transitioning from college to her first job. 

When millennials entered the workforce en masse around 2008, companies started to seek Lindsey out to help them understand this new generation of workers. Her research, writing and consulting experience made her a sought after speaker and author of several best-selling books. Lindsey brings a unique understanding of generational differences and how those differences play out in the workplace. Her keen insights and practical advice have helped millions of employers and job-seekers alike. 

We were excited to talk to her about how her learnings can help employers improve their benefit programs. Here are a few of the insights Lindsey shared with us. 

Insight #1: Understand generational differences to create better benefit programs. 

For the first time in history we have five generations in the workplace at the same time. That’s not because more young people are entering the workplace, it’s because people are working longer than ever before. People are succeeding and thriving for longer than in the past. Younger people are having to think about a career path that’s forty or fifty years long, and jobs that would have been available because of retiring workers are not available anymore. This all means that we have employees in a wider variety of life stages, and we need to adjust our benefit programs to accommodate the full spectrum of their needs. 

The COVID-19 pandemic brought a lot more attention to how people’s home circumstances impact their work. We saw that we can’t just look at somebody’s age to understand what they need. We have to look at their lifestage and their personal situation. Suddenly managers could see employees who were distracted by toddlers running around or employees who were lonely and isolated in tiny apartments in urban areas. They started to see how certain employees may need different types of support. 

As we move forward, it’s important to acknowledge that people have family circumstances that shape their home environments and their benefits needs, so the workplace needs to have some built-in flexibility and empathy for that. Understanding generational and lifestage differences can help employers create better benefits and a better place to work. 

Insight #2: Employees need carefully tailored benefit choices.

In past episodes we’ve heard from leaders across the insurance industry about how important it is to tailor benefits to the changing needs of today’s employees. As the pandemic highlighted, employees are going to need options both for their benefits and with workplace policies so they can do their best work. 

Some people will want to work remotely, people may want a hybrid schedule, and others will want to come into the office every day. Employers are often looking for one-size-fits-all solutions, but according to Lindsey, they simply don’t exist. Expanding options around benefits, support, and the ways we work, will be important, and since choices can also be overwhelming, options should be tailored to the needs of specific groups.

Generational differences are a helpful lens to look through because they help you figure out people’s unique pain points and expectations. Each generation has certain shared experiences that influence what they expect at work. Now we have a broader set of experiences to draw on to understand how we want to work and the support we need. Likewise, companies have more experience with different work styles and a greater awareness of employees personal needs. Employers should use this information to develop flexible programs and policies that make their whole team happy, healthy and productive. 

Insight #3: Leaders should keep cultivating transparency.

During the pandemic, Lindsey observed that leaders who were accessible to their employees and were transparent were able to navigate changing circumstances really well. Leaders who hid from their employees did not do well. The best leaders are transparent, empathetic, and accessible, and the pandemic made that clearer than ever. It can be easy to let transparent communication and connecting with employees fall by the wayside in the midst of a stressful season, but we all have a chance to get back to basics and think about how to best serve our teams—particularly when it comes to communicating about their benefit choices.

Hear more insights from Lindsey in the full episode: 

Lindsey’s Inspiration for Her New Book Recalculating

Early in the pandemic when Lindsey’s travel schedule ground to a halt, she had a bolt of inspiration. The pandemic was a lot like when you take a wrong turn, she thought, and the GPS says “recalculating.” You can’t keep going the way you were going, but there is another way. Lindsey realized that job seekers and professionals in transition would need new guidance for how to navigate their careers during and after quarantine ended. 

To write this book, Lindsey started by talking to people about what they were doing during the pandemic and how they were coping. She found a way to recalculate from a live speaking career to online coaching and writing this book, and she teaches her readers how to do the same no matter what career stage or industry they’re in. Grab a copy via any of these booksellers

We asked Lindsey about a book that was an inspiration in her leadership path. She recommended the book Mindset by Carol Dweck, which focuses on the benefits of having a growth mindset. A growth mindset means you can see ways to change, grow, and develop in everything you approach. That helped Lindsey see that the pandemic wasn’t a dead end, but rather a pivot that helped her find new opportunities for growth.  

If you’d like to connect with Lindsey you can visit her website at Note, this episode is for informational and educational purposes only. Lindsey Pollak not endorsed, affiliated with, nor compensated by Greenhouse Life Insurance Company.

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